P-Anisidine → 1-(2-Methoxyethyl)-3-[(4-methoxyphenyl)amino]-4-phenyl-1H-pyrrole-2,5-dione

HRID 2113750Notes

Reaction equation

Cl[C:2]1[C:3](=[O:18])[N:4]([CH2:14][CH2:15][O:16][CH3:17])[C:5](=[O:13])[C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH3:19][O:20][C:21]1[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=1>CN(C=O)C>[CH3:17][O:16][CH2:15][CH2:14][N:4]1[C:5](=[O:13])[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[C:2]([NH:25][C:24]2[CH:26]=[CH:27][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)[C:3]1=[O:18]

Participants

Conditions

Temperature: 150 °C

Procedure

3-Chloro-1-(2-methoxyethyl)-4-phenyl-1H-pyrrole-2,5-dione (0.20 mmol, 53 mg) and 4-methoxyaniline (0.48 mmol, 59 mg) were dissolved in DMF (1 mL). The mixture was heated in a microwave reactor at 150° C. for five min.min. After cooling, the reaction mixture was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN) to give 15 mg (21%) of the title compound. 1H NMR (400 MHz, CDCl3): δ 7.27 (bs, 1H), 7.13-7.04 (m, 3H), 7.00-6.96 (m, 2H), 6.61-6.50 (m, 4H), 3.80 (t, J=5.6 Hz, 2H), 3.67 (s, 3H), 3.62 (t, J=5.6 Hz, 2H), 3.36 (s, 3H).

Workup

temperatureAfter cooling
customthe reaction mixture was purified by HPLC (95% 0.1M ammonium acetate buffer: 5% CH3CN→100% CH3CN)

Sources & evidence

ORD record: ord-ae113fd7e3164138b4fcd5d0abfe7daf
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07432288B2

Reaction notes

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